In vitro effects of benzimidazole/thioether-copper complexes with antitumor activity on human erythrocytes

Suwalsky, Mario; Castillo, Iván; Sánchez-Eguía, Brenda N.; Gallardo, María José; Dukes, Nathan; Santiago‐Osorio, Edelmiro; Aguiñiga, Itzen; Rivera-Martínez, Ana Rocío

doi:10.1016/j.jinorgbio.2017.10.009

Cited by 12 publications

(5 citation statements)

References 33 publications

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“…According to the Sheetz and Singer hypothesis, echinocytes are created when the modifying compound is concentrated mainly in the outer lipid layer, while stomatocytes are formed when the substance is accumulated in the inner lipid layer of the RBCs membrane (Sheetz and Singer 1974 ; Iglic et al 1998 ; Lim et al 2002 ). It was also observed that when the concentration of echinocytogenic molecules is further increased, spherocytes began to appear and finally the process of hemolysis begins (Brecher and Bessis 1972 ; Isomaa et al 1987 ; Hägerstrand and Isomaa 1989 , 1992 ; Iglic et al 1998 ; Suwalsky et al 2009 , 2016 , 2017 , 2018 ; Bonarska-Kujawa et al 2012 , 2014 ). In accordance with the hypothesis presented above, investigated complexes are expected to be localized mainly in the outer lipid monolayer of the erythrocyte membrane.…”

Section: Resultsmentioning

confidence: 99%

“…It was also observed that when the concentration of echinocytogenic molecules is further increased, spherocytes began to appear and finally the process of hemolysis begins (Brecher and Bessis 1972; Isomaa et al 1987; Hägerstrand and Isomaa 1989, 1992; Iglic et al 1998; Suwalsky et al 2009, 2016, 2017, 2018; Bonarska-Kujawa et al 2012, 2014). In accordance with the hypothesis presented above, investigated complexes are expected to be localized mainly in the outer lipid monolayer of the erythrocyte membrane.…”

Section: Resultsmentioning

confidence: 99%

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An In Vitro Study of the Effect of Cytotoxic Triorganotin Dimethylaminophenylazobenzoate Complexes on Red Blood Cells

et al. 2018

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Interactions of tributyltin (TBTA) and triphenyltin (TPhTA) 2-[4 (dimethylamino)phenylazo]benzoates, showing promising cytostatic activity against tumor cells, with erythrocytes and with erythrocyte membranes and model lipid membranes have been investigated. The effect of TBTA and TPhTA on the erythrocyte and its model membrane was investigated by the microscopic and spectroscopic methods. Interaction of tin complexes with the membrane was determined on the basis of hemolytic activity, changes induced in the shape of erythrocytes, as well as physicochemical parameters of the membrane, such as fluidity. The studies showed that the compounds in higher concentration induce hemolysis; however, TBTA is more toxic than TPhTA. Both TBTA and TPhTA induce morphological alterations in red blood cells—from discocytes to spherocytes and from discocytes to echinocytes. The results suggest that investigated complexes interact with the erythrocyte membrane, change its properties, and probably locate themselves in the hydrophilic part of the membrane, which agrees with conclusions drawn from investigation of erythrocyte membranes and model lipid membranes with the help of fluorescence and infrared spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

An In Vitro Study of the Effect of Cytotoxic Triorganotin Dimethylaminophenylazobenzoate Complexes on Red Blood Cells

et al. 2018

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“…This can be due to azomethine bonding as well as the presence of lone pair electrons within the nitrogen atom. [2][3][4][5][6][7][8][9] The anticancer effect and bioactivity of Schiff base ligands are improved by the complexation to a metal ion. [10][11][12][13][14] In addition, investigation of coordination complexes can help fine expansion in inorganic biochemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

Parvarinezhad

Salehi

Malekshah

et al. 2022

Applied Organom Chemis

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Metal (II) complexes of Cu (II) (1), and Ni (II) (2) with Schiff base derived from 4‐amino‐antipyrine were synthesized. These complexes were fully characterized by FTIR, and UV–Vis spectroscopies, crystallography, and cyclic voltammetry. Crystal structures of these two complexes were mononuclear. Furthermore, complex Cu (II) (1), of [CuII(H2L1)(NO3)] composition, is 4‐coordinated in a square‐planar environment. Complex Ni (II) (2) is six‐coordinated in an octahedral geometry and can be described as [NiII (H2L2)2]; this crystal structure additionally contains solvent—DMSO molecule. The experimental structural models are interpreted by Hirshfeld surface analysis, density functional theory calculations, Molecular Electrostatic Potential, and the atoms in molecules method. Density functional theory calculations support all experimental results, as well as predict the correct structure of complexes. In addition, the types of interactions in the structure of the complexes were identified by Hirshfeld surface analysis, and molecular electrostatic potential was used to confirm the formation of these interactions, and the results of these studies are consistent. Then the theory of atom in molecule was performed, which predicts the type of interaction of the ligand metal non‐covalently with ionic nature. To determine the mechanism of adsorption of complexes on chitosan, a Monte Carlo adsorption locator was utilized. The adsorption process of complex [CuII (H2L1)NO3]and [NiII(H2L2)2(C2H6SO)] in the aqueous phase on CS was calculated by Monte Carlo adsorption locator. The results showed complex [NiII(H2L2)2(C2H6SO)] had a high binding efficiency on CS compared with complex [CuII (H2L1)NO3]. Moreover, the anticancer effects of ligands and complexes toward MTT assay against SW480 cancer cell lines were investigated. The biological activity results illustrate that the ligands and complexes have anticancer activity. Molecular docking studies were also carried out for both complexes to find their binding affinity with protein B‐cell lymphorna (BCL‐2, PDB ID: 4LXD).

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“…The mechanism of this activity can be explained by a determination of interactions between antineoplastic compound and the cell membrane and its effect on the biophysical parameters of membranes. The knowledge of this research is an important tool for better understanding the therapeutic activity of drugs and their toxic effects, because these processes may be related to the effect of the antitumor drug on the membrane [31,32]. This can play a significant role also in the future design of new more active drugs and delivery systems as well as the identification of new membrane targets.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes

et al. 2020

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The aim of this work was the examination of biological activity of three selected racemic cis-β-aryl-δ-iodo-γ-lactones. Tested iodolactones differed in the structure of the aromatic fragment of molecule, bearing isopropyl (1), methyl (2), or no substituent (3) on the para position of the benzene ring. A broad spectrum of biological activity as antimicrobial, antiviral, antitumor, cytotoxic, antioxidant, and hemolytic activity was examined. All iodolactones showed bactericidal activity against Proteus mirabilis, and lactones 1,2 were active against Bacillus cereus. The highest cytotoxic activity towards HeLa and MCF7 cancer cell lines and NHDF normal cell line was found for lactone 1. All assessed lactones significantly disrupted antioxidative/oxidative balance of the NHDF, and the most harmful effect was determined by lactone 1. Contrary to lactone 1, lactones 2 and 3 did not induce the hemolysis of erythrocytes after 48 h of incubation. The differences in activity of iodolactones 1–3 in biological tests may be explained by their different impact on physicochemical properties of membrane as the packing order in the hydrophilic area and fluidity of hydrocarbon chains. This was dependent on the presence and type of alkyl substituent. The highest effect on the membrane organization was observed for lactone 1 due to the presence of bulky isopropyl group on the benzene ring.

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In vitro effects of benzimidazole/thioether-copper complexes with antitumor activity on human erythrocytes

Cited by 12 publications

References 33 publications

An In Vitro Study of the Effect of Cytotoxic Triorganotin Dimethylaminophenylazobenzoate Complexes on Red Blood Cells

An In Vitro Study of the Effect of Cytotoxic Triorganotin Dimethylaminophenylazobenzoate Complexes on Red Blood Cells

Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes

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